Isolation of a Major Metabolite (i-OHAP) of Aprindine and Its Identification as N-[3-(N, N-Diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol

Abstract

i-OHAP, a major metabolite of aprindine (AP), was isolated by TLC from rat feces and identified as N-[3-(N, N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol, based on ¹H-NMR, the H-H correlation spectroscopy (COSY) spectrum, MS and LC-MS. Its structure was also confirmed by comparison with the synthesized compound. The hydroxy group of i-OHAP was located at the 5-position of the indan ring. AP is a prochiral compound, and the metabolism of AP to i-OHAP was stereoselective. The ratio of (+)/(-)-i-OHAP in rat feces and in human urine was about 5 and 15, respectively.